1,3,5-Trinitrobenzene (CHEM000094)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2009-03-06 18:58:05 UTC
Update Date2026-03-26 21:45:33 UTC
Accession NumberCHEM000094
Identification
Common Name1,3,5-Trinitrobenzene
ClassSmall Molecule
Description1,3,5-Trinitrobenzene (1,3,5-TNB) is a synthetic substance that is used in explosives. (2)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • T3DB toxins
Contaminant Type
  • Aromatic Hydrocarbon
  • Explosive Agent
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3,5-TrinitrobenzolChEBI
S-TrinitrobenzeneChEBI
Sym-trinitrobenzeneChEBI
TNBChEBI
2,4,6-TrinitrobenzeneHMDB
Chemical FormulaC6H3N3O6
Average Molecular Mass213.105 g/mol
Monoisotopic Mass213.002 g/mol
CAS Registry Number99-35-4
IUPAC Name1,3,5-trinitrobenzene
Traditional Nametrinitrobenzene
SMILES[O-][N+](=O)C1=CC(=CC(=C1)[N+]([O-])=O)[N+]([O-])=O
InChI IdentifierInChI=1S/C6H3N3O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H
InChI KeyUATJOMSPNYCXIX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzenes
Alternative Parents
Substituents
  • Nitrobenzene
  • Nitroaromatic compound
  • Organic nitro compound
  • C-nitro compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical Roles
Physical Properties
StateSolid
AppearanceYellow solid.
Experimental Properties
PropertyValue
Melting Point121.5°C
Boiling PointNot Available
Solubility0.278 mg/mL at 15 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP1.54ALOGPS
logP1.79ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)16.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area137.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.03 m³·mol⁻¹ChemAxon
Polarizability15.99 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0090000000-a30aa9a40b9ab37a15f6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-398ffea8a5845e630c77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0590000000-e860cd06a78af86dc521Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-0690000000-02bd0a06e80146e0ec84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-cc780cd5655f0b1ffd2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-a0c65596d90080d48193Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fr-1190000000-885b4046ba5937ce4d6dSpectrum
MSMass Spectrum (Electron Ionization)splash10-03di-9260000000-c6b318055501d919d6b7Spectrum
Toxicity Profile
Route of ExposureOral (2); inhalation (2) ; dermal (2)
Mechanism of ToxicityIn the red blood cell, 1,3,5-TNB induces formation of methemoglobin, leading to cyanosis. Reduction of the nitrogroup(s) of 1,3,5-TNB produces reactive nitroaromatic radical anions which redox cycle to produce other reactive species such as superoxide anion. Redox cycling of these intermediates probably causes the methemoglobinemia. 1,3,5-TNB may also exert neurotoxic effects by damaging the blood-brain barrier.(2, 1)
Metabolism1,3,5-Trinitrobenzene is absorbed via oral, inhalation, and dermal routes and is believed to penetrate the red blood cell membrane. The metabolism of 1,3,5-TNB includes both oxidative and reductive biotransformations, followed by conjugation. The main route of excretion of 1,3,5-TNB metabolites is the urine. (2)
Toxicity ValuesLD50: 250 mg/kg (Oral, Rat) (3) LD50: 32 mg/kg (Intravenous, Mouse) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources1,3,5-Trinitrobenzene is used in explosives. Waste discharges from army ammunitions plants or other chemical manufacturers are the primary sources for release into the air, water, and soil. (2)
Minimum Risk LevelNot Available
Health EffectsChronic exposure to 1,3,5-trinitrobenzene can cause a reduction (or loss) in the number of red blood cells (anemia). 1,3,5-TNB may also have neurotoxic effects. (2, 1)
SymptomsExposure to high concentrations of 1,3,5-trinitrobenzene can reduce the ability of blood to carry oxygen and can cause skin bluishing. Other symptoms nclude headache, nausea, and dizziness. (2)
TreatmentTreatment is mainly symptomatic and may include gastric lavage and/or the administration of activated charcoal. Benzodiazepine may be administered if seizures occur. If methemoglobinemia is evident, 1 to 2 mg/kg of 1% methylene blue should be administered via IV. (4)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0244187
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link1,3,5-Trinitrobenzene
Chemspider ID13873689
ChEBI ID48113
PubChem Compound ID7434
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.